9 revealing job interview questions top CEOs ask – answered

If you’re the one doing the interviewing of a potential employee — you might just find some great questions in here to use yourself.

Photo: WOCinTech via Flickr

CEOs are notoriously eccentric, but they got where they are by picking the brightest people to join them. When it comes to either job interviews, why not base your preparation on some of their favorite questions? Here are some questions CEOs really ask — and how to answer them. (Oh and hey, if you’re the one doing the interviewing of a potential employee — you might just find some great questions in here to use yourself.)

Neil Blumenthal, CEO of Warby Parker’s favorite interview question

1. What do you like to do for fun?

According to a 2013 interview with The New York Times, this CEO loves this job interview question because it “always speaks volumes of who that person is. Blumenthal said that he also often asks, “What was a recent costume you wore?” Why?

“The point isn’t that if you haven’t worn a costume in the last four weeks, you’re not getting hired,” he says, “It’s more to judge the reaction to that question. Are you somebody who takes yourself very seriously? If so, that’s a warning sign to us. We want people to take their work seriously but not themselves.”

How to answer this style of question: This is a culture fit question through and through. The idea behind these is that you should know the company and have considered whether you’d make a good addition to the personalities there. The best way to prepare for these sorts of questions is to do your research thoroughly. Because if you really loved Warby Parker, shouldn’t you know that they like their team to have a little fun? (I mean, those glasses look fun).

Elon Musk, Founder of Tesla and SpaceX

2. “Tell me the story of your life and the decisions that you made along the way and why you made them and also tell me about some of the most difficult problems you worked on and how you solved them.”

Yeah, cool, Elon. No problem. At a 2017 World Summit in Dubai, CNBC reported that Musk also said that, ” ‘People that really solved the problem, they know exactly how they solved it they know the little details’ while who are ‘pretending’ go into just one level of detail ‘then they get stuck’.”

How to answer this style of question: Know yourself and prepare to answer questions about problems and mistakes — they come up more frequently than most job interviewees expect. Also, feel free to pause and linger on a question when it’s hard-hitting like this. Got a feeling even Elon Musk would rather you slowwwww down before answering than “pretend” or “get stuck.”

Melanie Whelan, CEO of Soulcycle

3. Tell me about your background.

A deceptively simple and all-too-common interview question, Whelan goes with this for a very good reason. She explains it like this: “It’s a great way to warm up any conversation, and it really helps me understand how you communicate. Are you linear, concise and direct? Or are you a storyteller? Are you entertaining? Do you go off on tangents?”

4. Tell me about this [XYZ] career decision or career transition.

Apparently, Whelan also likes to ask questions about career transitions to see how interviewees approach them. “Were you running away from something or toward something, and how do you frame that?”

How to answer this style of question: Know your personal pitch and know how to tell a story well. That includes being able to talk about gaps in your resume or shifts between industries. If you’re not comfortable talking about yourself, you need to work on it either with friends or by joining a local Toastmasters or something of the sort. This is a type of public speaking and how you articulate your background is absolutely key.

Laszlo Bock, Former Google Human Resources Chief

5. Give me an example of a time when you solved an analytically difficult problem.

OK so Bock isn’t a CEO exactly, but that’s a pretty high-level executive title. This is what you might call a “behavioral” interview question and according to Inc., it’s a similar style to Musk’s. Here’s how Bock explains behavioral interviewing to the New York Times: ” ‘you’re not giving someone a hypothetical, but you’re starting with a question like, ‘Give me an example of a time when you solved an analytically difficult problem.’ ” He added, “You get to see how they actually interacted in a real-world situation, and the valuable ‘meta’ information you get about the candidate is a sense of what they consider to be difficult.”

How to answer this style of question: Don’t be afraid to get real, in fact, that’s the point. Pull an actual example from the last few months. If you’re not self-reflecting on your work, you should be. One way to do this is to start keeping a work journal of your successes and failures right now.

Lori Dickerson Fouché, CEO of Group Insurance at Prudential Financial

6. If you find yourself in situations where they’re not going the way you want them to, what do you do?”

According to an interview with the New York Times, this — and other questions around difficult moments—is how Fouché can tell how a candidate conducts herself under pressure. She also asks:

7. What kind of cultures do you like to work in? Where do you excel? How do you excel?

Says Fouché, “you have to find a way to navigate and negotiate to an end result. It could be a winding path. So I make sure that people feel like they know how to do that, and do it in a way that is respectful of the system.”

8. Describe some difficult leadership situations and how you managed people through them.

This is a question she asks for higher level positions to gauge “how they make their own hiring and firing decisions.”

How to answer this style of question: These may seem like different questions, but according to Fouché, each focuses on “perseverance and resilience” — great qualities to have especially at the bigger companies where she’s worked. Approach these with a critical eye. Explain how you work, but also why. And don’t be afraid to mention a moment where you misstepped early on and how you learned to something essential about how you work or how you lead.

Rick Goings, CEO of Tupperware

9. A Curveball: “I Ask How They Were Treated.”

No, this isn’t a question for you. It’s for the receptionist who you checked in with and maybe the person who rode the elevator up with you, too. Goings explains that the best way to understand a job candidate is to ask people how they behaved when it didn’t occur to them that anyone was paying attention. It’s a way to get “a sense of the ‘non-cognitive skills’ that good leaders need to manage and inspire teams.

How to do this right: Treat everyone like they could be the company’s CEO. Honestly, when our CEO, Lauren worked at Hulu, she’d always ask the receptionist how candidates had behaved, too. And especially in startups, you never know if the woman who’s sitting at the front desk is actually the founder, just checking on something.